(1S,3R,4R,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

• ChemBase ID: 157574
• Molecular Formular: C25H24O12
• Molecular Mass: 516.45086
• Monoisotopic Mass: 516.12677621
• SMILES: c1cc(c(cc1/C=C/C(=O)O[C@@H]1C[C@@](C[C@H]([C@H]1O)O)(C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)O)O
• Canonical SMILES: O=C(O[C@@H]1C[C@@](OC(=O)/C=C/c2ccc(c(c2)O)O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/t19-,20-,23-,25+/m1/s1
• InChIKey: YDDUMTOHNYZQPO-BBLPPJRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4R,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1S,3R,4R,5R)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
• Synonyms: (1S,3R,4R,5R)-1,3-Bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-4,5-dihydroxycyclohexanecarboxylic acid; 1,3-Dicaffeoylquinic acid; 1,5-Dicaffeoylquinic acid

Database IDs

• CAS Number: 19870-46-3
• MDL Number: MFCD13196505
• PubChem SID: 162251711
• PubChem CID: 6474640

CALCULATED PROPERTIES

• Acid pKa: 3.184533
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -0.13374609
• LogD (pH = 7.4): -1.3031974
• Log P: 2.1582303
• Molar Refractivity: 126.7642 cm^3
• Polarizability: 48.731434 Å^3
• Polar Surface Area: 211.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Impurities: ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C25H24O12

DETAILS

Sigma Aldrich - 16917

Biochem/physiol Actions
Phenolic compound found in artichoke. Antioxidant and choleretic properties. Potential immunosuppressive agent.